How to Dress More Stylishly for the Fall Weather

By Jack Prenter / September 30, 2017
Dressing for the Fall Men's Style

Fall is here gentlemen and up in Canada it’s cooling down extremely quickly, with snow expected before December. Coming out of Summer can be difficult and the change in clothing is huge, it’s time to trade those shorts for a sweater or an overcoat and prepare for the cold.

Layering Effectively

One of the most important tips for dressing for Fall is layering effectively. What this means is wearing multiple layers of clothing on a single body part, for example, a polo and a sweater, rather than just the polo.

In this way you can still keep some of your warmer weather clothes that you’ve been wearing in Summer, in circulation.

A lot of men find that they usually get cold on their upper body, because they often wear full length pants, but only shorter sleeve tops. Therefore, because it’s not extremely cold yet it’s often best to primarily layer on your upper body.


Fall is the season of the sweater, possibly one of the greatest inventions of all time, which can go with almost anything and is still considered to be an acceptable piece in nicer venues. Combining a sweater with a polo or cloth shirt can be a great preppy look for Fall.

Sweaters can be found in a huge variety of styles and also materials, which is great because of the huge variety in weather during Fall. On colder days it’s best to opt for a thick wool, whereas, those warmer days are ideal for a thin cotton sweater.

When it comes to style there are four main kinds to consider; rounded collar, v-neck, shawl and quarter zipper. The rounded collar sweater is generally the least fashionable and also relatively difficult to match with other pieces.

If you’re going for a preppy look then the quarter zipper is ideal, especially in a nice neutral colored cashmere. The shawl collar can be extremely casual, perfect with jeans and boots, and the v-neck is fantastic with an open collared dress shirt.

Overall, a nice range of sweaters to choose from is a must if you want to be able to transition into Fall, feel comfortable and still look incredible.

Quarter Cotton Zip Sweater

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Depending on where you live you’re either never going to need a coat in Fall, or you might even need a relatively heavy and thick one. But for most people Fall is the ideal time to pull a light coat out of your closet, especially if you’re going out for dinner or drinks in the evening.

It’s our belief that a classic neutral colored overcoat in a wool blend is a must have, because it offers you a decent level of warmth and can easily be worn up or down, depending on the event. Overcoats can also stretch to be worn with a sweater and other layers underneath.

Coats are a tough topic for stylish men, because unless you enjoy street wear, there are very few types of coats that can be worn smartly and also fashionable. In most cases you’re restricted to pea coats, chesterfields, leather jackets and trench coats.

Our personal favorites are the pea coats and leather jackets, because they are extremely versatile and completely timeless. Over the past four decades both of those coats have been worn by the most stylish men of the time and this is only going to continue into the future.

Black Pea Coat

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As the Summer weather has faded away, so have our loafers and sandals, only to be replaced by sneakers, dress shoes and the greatest of all, the classic boot. Is there anything greater than a boot? That sturdy feeling and robust build is hard to compare to, combined with a rugged yet stylish appearance that reminds of us of Hollywood stars from the 60’s.

The boot comes in many different shapes and sizes, but the ideal boot for the Fall is the Chelsea boot, no questions asked. It combines everything great about a boot; the thickness, the heal and the leather, with a chic and yet timeless appearance.

In most areas Fall is characterized by dry and cold weather, which makes Chelsea boots a perfect pick. Once the rain and snow starts they aren’t as useful, but for Fall they make an ideal footwear choice.

Black Leather Chelsea Boots

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Tone Down the Color

Our final tip for dressing in Fall is to tone down the colors that you’re wearing. Generally, Summer is all about the bright color combinations, blinding whites and beautiful pastels, but Fall is normally best for grey, charcoals, reds, blacks and browns.

These colors not only match the natural surroundings, but they also fit the relatively somber mood of Fall, after all, nature is shedding its fruit. Hopefully, that wasn’t too hippy for you.

Regardless, each season has its own color palette and by disregarding that you will end up looking entirely out of place.

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